How to pick up a cougar?

Many guys want to know how to attract and pick up cougars, so this article is my personal story about picking up a cougar.


I had just finished up an underwhelming trip to South Beach. Rather than get a good nightʼs sleep, I venting at how overrated Miami bars and clubs are on online message boards (did I mention how cool I was?).

Finally, I got off the hotel computer, packed my things and headed for the airport. I originally went to Miami in hopes of chasing and getting more ass than I ever had before, but ironically, I would get laid in the process of leaving Miami.

I should note that at this point, meeting women was the furthest thing from my mind. I hadnʼt showered, had only slept for about three hours, and only eaten a shitty sandwich for breakfast. I know the advice say “always look and feel your best,” well, I wasnʼt even close.

I get to the gate and plop down in a seat waiting to board. I look around and actually see a few hot girls. I always like to check out girls who Iʼll be flying with, because if youʼre lucky enough to sit next to them, they can be an easy pick up.

I saw a few hotties. One had her back to me standing near the check-in counter: slim, athletic body, gorgeous tan, nice rack; although I could not see her face, her body was quite nice though.

I get on the plane, and lo and behold, Iʼm sitting next to the woman I had checked out, but I notice when I look at her face: sheʼs old. Not like, OLD old, but sheʼs definitely MILF-territory, mid to late thirties. Regardless, I proceed to pass out next to her with my iPod going. I was asleep so fast that I donʼt even remember take-off.

Couple hours later I wake up and HBCougar is watching some movie on her laptop. My iPod dies so I lazily sit there and stare at her screen.

Itʼs some cheesy thriller from the 80ʼs with young Kurt Russell and Ray Liotta apparently fighting over some damsel in distress.

I watch for a good 20-30 minutes until the apparently evil Ray Liotta is trying to rape the babe, but then Kurt Russell shows up to rescue her and they end up fighting a bloody battle in the kitchen.

At this point, the plane edges downward and thereʼs an announcement to prepare for landing. The stewardess comes by and asks HBCougar to turn off her laptop. HBCougar shuts down the movie and takes off her earphones.

Iʼm still kind of in a haze, and although Iʼm definitely attracted to HBCougar (any of my friends will tell you, I kind of have a thing for older women), so I figure I should talk to her.

Me: “Damn, now weʼll never know if the bad guy wins or not!”

HB: “He ends up getting beaten up by a frying pan, Iʼve seen it before.”

Me: “I havenʼt. Iʼm disappointed, that was an awesome movie.” (said very sarcastically) HB: *laughs* “Yeah, right.”

Me: “Was that Kurt Russell?”

HB: “Yeah, when he was like 15. I just bring these cheesy movies around because I travel so much, I get bored on airplanes.”

Sheʼs hooked, and I begin to consciously hit on her.

Me: “What do you do?” (Wow, how original, Mark)

HB: “Iʼm a sales rep.”

Me: “Selling…?”

HB: “Online advertising, I meet with clients all over the US and Europe. We have over 600 clients in the travel and tourism industry.”

A while back I was talking to an older woman in her 30ʼs and we were talking about why 30-something women and 20-something men hook up so often.

She gave me a great nugget of wisdom. She said that dating in your 30ʼs often revolves so much around your career and status that a lot of the fun is drained from the relationship or interaction.

Women begin basing attraction on success and wealth as much as they do on personality and emotion. She said that women in their 30ʼs love the excitement that guys in their 20ʼs bring — the guys just want to have fun (and sex), and these women miss that, so they are often drawn to them.

So anyway, this woman is going on about her job, about how much she travels, her clients, what she sells, etc. Fuck that, welcome to MY reality.

Me: “Oh… my… God!”

HB: “What?”

Me: “Youʼre responsible for all those fucking pop-ups ads on my computer, arenʼt you? I hate you.”

HB: *laughs* “No, we donʼt do pop-ups.”

Me: “Oh, thank God… Iʼd have to stop talking to you.

HB: *laughs*

Me: “So, youʼre in Boston for business?”

HB: “Yeah, a meeting tomorrow morning, then I fly back out tomorrow night.”

Weʼre landing in like two minutes and asking for her number crosses my mind, and I suppose I still have some limiting beliefs because I just figured me going out with her wasnʼt plausible. She doesnʼt have enough time, right?

Stupid me, because sheʼs giving me some eyes now, I notice she has no ring on her left hand, she keeps re-initiating the conversation.

HB: “Where are some good places to eat in Boston?”

Me: “Umm… Boston has great Italian food. You should check out the North End, lots of good Italian food there.”

HB: “You donʼt have any specific recommendations?”

Me: “Uhh…. no, not really.”

HB: “Well then, what good are you to me?”

Me: *laughs* “Apparently not much, I guess I donʼt eat out much.”

HB: “Well then, what about bars? Where could I get a martini tonight?”

Me: “Well, Sundayʼs are kind of slow, but where are you staying?”

HB: “The Fairmont in Copley Plaza.”

Me: “Oh, there are tons of good places around there.”

Sheʼs basically begging me to ask her out here, but Iʼm still being thick-headed and not confident enough, despite her hints. But this brings me to:

Why I Love Older Women, Reason #1: They Get to the Point.

HB: “Well, you should come out and show me around, get a drink with me.”

Me: (caught a bit off-guard, trying not to stutter) “Yeah. Thatʼd be great.”

She gives me her number and even corrects me when I mess it up. I already had an entry with her name, so my phone popped up a big red ʻXʼ with “WARNING” under it telling me to change the name of the entry.

HB: “Uh oh, your phone is warning you.”

Me: “Yeah, itʼs telling me ʻDonʼt call this woman, sheʼs bad newsʼ.” HB: *laughs real hard* “I need a phone that smart.”

We chit-chat a bit more and I ask if she knows anyone else in Boston.

She says she has a friend here, but “he has a girlfriend now, so he said he canʼt see me.” I am SO getting laid tonight.

Few hours later, Iʼm in a swanky restaurant bar on Newbury with her and her co-worker. Her co-worker is married and a bit younger than her, a pretty blond from NYC. I tell them that I just spent over two weeks away to go to Texas and Miami.

The co-worker asks me how I used up so much vacation. I respond, “Easy, itʼs called being unemployed.”

Normally, one would be embarrassed about this.

But Iʼm young, fuck it. I emphasized the freedom, opportunities, and potential, bringing them into a more positive frame. They cooed, “Yes, you have your whole life ahead of you. Iʼm jealous.”

Next came the age-guessing game. They asked me straight-up, but I toyed around with them first. Eventually, I give in and it comes out that Iʼm 23. Cougar looks over at her coworker and says bluntly, “Iʼm a sicko.”

Turns out Cougar is 35.

I have a couple beers in me and my game is clicking on all cylinders now. I start directing the conversation about places weʼve all visited before, and meanwhile I egg on Cougar with playful “old lady” jokes. At one point she says:

HB: “You know, technically, Iʼm old enough to be your mother.”

Me: “Technically, you could call me ʻDaddyʼ too.”

HB: *laughs, stunned look on her face* “What makes you think that? I only talked to you for 10 minutes on an airplane!”

Me: “Yeah, but it was quality, not quantity.”

Next came one of the biggest compliments I had ever received up until that point in my life.

HB: *pauses* “Itʼs kind of scary to see so much confidence in a 23 year old.”

Me: “I donʼt think itʼs a bad thing.”

HB: *looks me in the eye and smiles* “Definitely not.”

I get up to go piss and when I come back the co-worker says sheʼs going to go back to the hotel — this is girl-code assuring me that Iʼm in. I suggest a new bar to Cougar and she agrees.

We go to City Bar. Itʼs a nice calm atmosphere with a lot of older business-types at the bar. We sit down at a table/booth, me in the booth, her in the chair across from me.

HB: *looks around* “Do you feel a bit young in here?”

Me: *laughs, pointing to old people at the bar* “Do YOU feel young in here?” HB: *laughs* “Yes, actually I do.”

We small talk for a bit, and my dumb ass self takes like 10 minutes to realize that her sitting across from me is a logistical problem for escalating purposes. But luckily:

Why I Love Older Women, Reason #2: Theyʼre Forgiving of your Mis-steps

HB: “So, when are you going to ask me to sit next to you?”

Me: “Uhh…. yeah, I was actually just thinking about that.”

HB: *gets up and sits next to me* “What took so long?”

Me: “Umm… I guess I was thinking of just the right thing to say.”

HB: “Youʼre going from sharing an airplane with me to a bed with me in six hours, then youʼll probably never see me again; just say it.”

Me: *stunned* “Uhh… yeah… I was getting there, I guess.” HB: “Youʼre cute.”

We start kissing and touching hard there in the booth. Soon, some young professionals come and sit at the table next to us. They look as if theyʼre in their late 20ʼs and are very drunk. One guy is very friendly and starts giving Cougar a lot of attention in front of me.

Drunk Guy: “So looks like things are going well for you two, this your first date or like the 10th?”

Me: “Like 12th or something. This is nothing new for us.”

Cougar LOVED this.

We started playing along and made up some story about how weʼre a long-distance couple and she travels to Boston between business trips every few weeks. I created some elaborate story about being in law school and considering moving down there with her after I graduate.

It was hilarious. She loved it. And she loved me for playing along. “Law school… nice touch,” she said later. I said, “I wanted him to ask how we met, so I could tell him on an airplane.”

We go back to her hotel room. I had never been in the Fairmont before, but holy shit, what a room. But the most important part: king-sized bed.

Why I Love Older Women, Reason #3: Theyʼre great lays.

Wow, this chick was awesome. I was in her room for less than 10 seconds when she just shoved me onto the bed and climbed on top of me. Iʼm usually not so big on foreplay with a lot of women, but I could have gone on for hours of foreplay with her.

She was just so sensual, responsive and playful. It was awesome. Then of course the sex came, and as with other 30-something women Iʼve been with, her technique was immaculate and she had some new positions I hadnʼt seen before. She moaned a lot and talked filthy, which is something I rarely get from girls my age. Very nice.

So even though she told me I wouldnʼt be sleeping there, I slept there. The next morning we talked briefly and I told her anytime sheʼs in Boston, I would love to hear from her.

She seemed a bit skeptical at first, as I think her previous Boston hook-up was flakey or a drama-queen or both. But I told her for me it was no bullshit, if she comes in, Iʼm her boy-toy for the night. She liked the idea and said sheʼd be in touch. I rode home at about 7:30am.

She sent me a text about 30 minutes later thanking me for the night and saying she couldnʼt believe sheʼs going to an important meeting on only four hours of sleep. This afternoon she sent another text saying her meeting went well and that Iʼll be hearing from here next time sheʼs in town.

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